PINTAIL is the only 84-foot Trumpy built in the desirable cruiser configuration. Built in 1963 and rebuilt in 1999, she is in beautiful condition with a double-planked mahogany hull. Featuring three generous staterooms, she sleeps six and offers a full-beam galley, raised pilothouse, and a spacious aft cockpit. Over the past 18 years, PINTAIL has become well known up and down the East Coast, particularly in Nantucket, Charleston, Jacksonville, and Palm Beach.

The PINTAIL Story

When John Trumpy & Sons closed its yard in 1974, the company had spent five decades building custom wooden motor yachts for America's most prominent families, including the presidential yacht Sequoia. Only two of those hulls reached 84 feet. PINTAIL, Contract #407, is one of them, and the only one built as a cruiser.

Six decades, four names, one boat. Commissioned by Col. David Flagstaff and launched as PINTAIL in 1963, she later carried the names ARAS, ACHASTES, and, from 1984, WISHING STAR under Michael Eagan, founder of Alamo Rent-a-Car. In 2024 her current owner returned her to the name she was launched with. Every owner in that chain kept her cruising, and each one invested in her. That continuity is rare in a wooden boat of her age, and it shows.

The rebuild that reset the clock. Between 1997 and 1999, PINTAIL underwent a $2.2 million rebuild that returned her to close to new condition. She was completely re-planked and is now double-planked in mahogany over oak frames. For a 1963 wooden yacht, this matters more than any single line in her equipment list: her structure is decades younger than her launch date.

Maintained by people who know Trumpys. In 2023 she completed an extensive yard period at Bristol Marine's Samples Shipyard in Boothbay Harbor, Maine, one of the few facilities in the country with deep experience in large wooden yachts. The work included a rebuilt aft cockpit deck and structure, reconditioned shafts and stabilizers, replaced tanks and pumps, and full hull paint. She has received annual service ever since, with upgrades continuing through 2026, from a remodeled galley to freshly inspected engines.

A familiar profile on the East Coast. For nearly two decades, PINTAIL has moved with the seasons between Nantucket, Charleston, Jacksonville, and Palm Beach. Dockmasters know her. Harbor neighbors photograph her. Few boats her age are recognized on sight in four different harbors; fewer still are ready to leave the dock the day they change hands.

PINTAIL is offered exclusively by Worth Avenue Yachts as her Central Agents. For showings, contact Jonathan S. Chapman.